Top 25 Greatest Heel Turns in Pro Wrestling History

Seth Rollins’ betrayal of his Shield teammates in favor of Evolution has drawn both shocked reactions and lukewarm reception from viewers. While it’s too early to stamp Rollins’ turn as a success or a failure, here’s a look at some of the wrestling history he’s up against, the twenty-five best shifts to the dark side ever.

25. Shawn Michaels Superkicks Hulk Hogan (July 4, 2005)

Would’ve meant more if WWE had stuck to Michaels’ heel run, but Hogan’s alleged refusal to lay down (ironic if you’re Michaels) killed the impact. Independence Day Raw ends with Hogan and Michaels passively celebrating a win, and Michaels landing Sweet Chin Music out of nowhere.

24. Terry Taylor Gradually Betrays Chris Adams (May 1987)

With UWF’s excitable Jim Ross calling each turn of the key, Taylor was conveniently absent for Hot Stuff International’s assaults on Adams, culminating with Taylor subtly allowing Adams to be pinned in a Tag Team Title defense. In a later singles match, Taylor piledrove an injured Adams on the floor, solidifying the turn.

23. Scott Steiner Lays Out Brother Rick (February 22, 1998)

It seemed as though by 1998, everyone on the planet save for Steve Lombardi had joined the nWo. That the eventual “Big Poppa Pump” did so by mauling brother Rick during a Tag Team Title defense against The Outsiders is only diluted by the notion that everyone seemed to turn in this era.

22. Sgt. Slaughter Spits on America, Sides with Iraq (August 1990)

A rather silly grab at kick-starting jingoism and Hulkamania in one swipe, Slaughter (now departed from the dying AWA) returned to WWE as a Saddam Hussein-sympathizer in the midst of the Gulf conflict, as Iraq invaded Kuwait. Bad taste, but it drew its share of heat.

21. Triple H Joins the Corporation (March 28, 1999)

Chyna’s two turns in one night was dizzying enough against the backdrop of a time-period where somebody turned every week. Still, Triple H Pedigree’ing X-Pac at WrestleMania XV was the launching pad of Paul Levesque’s rise to the highest office in WWE, via a relentless main event push for the next decade.

20. Bret Hart Condemns America (March 24, 1997)

With crowds divided between heroic Hart and anti-hero Steve Austin, ‘The Hitman’ goes on a post-WrestleMania tirade against American values, and what he felt was a decline in decency and morals. Shortly thereafter, Hart assaulted rival Shawn Michaels, solidifying a heel turn in America, while remaining a hero around the world.

19. Chris Jericho Wounds Shawn Michaels’ Eye (June 9, 2008)

After pointing out Michaels’ bouts of unfair play, and insinuating that Michaels enjoyed retiring Ric Flair at WrestleMania, Jericho attacks his long-time rival on the set of The Highlight Reel, and sends him face-first into his Jeri-Tron 6000 set piece, igniting the last WWE feud to intentionally feature blood.

18. Ted Dibiase Chooses Skandor Akbar Over Jim Duggan (May 1983)

Although more of a face turn for Duggan than anything, Dibiase gets heel-turn credit for sinking lower than the rule-breaking Rat Pack. Akbar’s “Devastation Inc” was anti-American and inherently more nefarious than anything Duggan and Dibiase had done with Matt Borne, so when Dibiase accepted Akbar’s offer, it kicked off a heated feud between sell-out Dibiase and proud patriot Duggan, foreshadowing their WWE personas.

17. Stone Cold Sells His Soul (April 1, 2001)

Would’ve ranked higher had Austin’s 2001 not been so creatively bankrupt and ill-received (to be fair, a lot of that’s on Austin for still wrestling like an outlaw ass-kicker). But the story is memorable: Austin enlists sworn enemy Vince McMahon to help him beat The Rock for the WWE Championship at WrestleMania X7, a match that Austin claimed he ‘had to win’.

16. Paul Bearer Betrays The Undertaker (August 18, 1996)

For nearly six years, Undertaker did not exist without Paul Bearer. Not a manager who needed a stable, Bearer happily co-existed with Undertaker as a package deal. That’s why during Undertaker’s Boiler Room Brawl with Mankind at SummerSlam, Bearer’s sudden turn, punctuated with an urn to Taker’s skull, was so shocking.

15. The Horsemen Leave Sting for Dead (February 6, 1990)

Sting found himself part of a babyface version of The Horsemen with Ric Flair and The Andersons, set to combat Gary Hart’s J-Tex Corporation. Sting, naive as he always was, made the mistake of challenging Flair for a World Title match, and was promptly beaten by his so-called friends. Sting injured his knee that night attempting to get revenge, but would go over on Flair for the gold at that year’s Great American Bash.

14. The Authority Excommunicates Daniel Bryan (August 18, 2013)

After cleanly going over on John Cena to become WWE Champion at SummerSlam, Bryan was faced with an eager Randy Orton, who was set to cash in his Money in the Bank briefcase. Then referee Triple H (a babyface at this point) Pedigreed Bryan, enabling Orton (also a babyface before these actions) to score the title. Thus, The Authority was born.

13. Owen Hart Kicks Bret’s Leg (Out of His Leg) (January 22, 1994)

Simmering since Survivor Series, Owen Hart stewed in brother Bret’s shadow, claiming to have been held back out of jealousy. Cooler heads seemed to prevail, and the brothers faced the Quebecers for the Tag Team Titles at the Royal Rumble. When the Harts lost by stoppage due to Bret’s injured knee, Owen engaged in the ultimate meltdown, concluding by kicking Bret’s bad knee and leaving in a huff.

12. Austin Idol Bloodies Jerry Lawler (January 4, 1987)

Moments before Lawler was set to challenge AWA Champion Nick Bockwinkel for the gold, friend Idol entered the ring and demanded that “The King” step aside. Lawler refused, and Idol busted him open. A week later, Idol and new friend Tommy Rich continued the onslaught, ending with Idol cradling Lawler’s head and passively bitch-slapping him. The payoff was a cage match in April 1987 where the loser got their head shaved, and a near-riot ensued.

11. The Rock and Shane McMahon Go Corporate (November 15, 1998)

Shane’s heel turn ranks as one of the most unexpected in the jaded internet era, as he refused to impartially count Steve Austin’s pin of Mankind in the World Title Tournament. Less than an hour later, Shane and father Vince screwed simpleton lackey Mankind in the finals in favor of their new corporate champion, The Rock.

10. Ric Flair Crosses Dusty Rhodes (September 29, 1985)

A different sort of ‘heel turn’, as Flair would hardly qualify as a babyface in this instance. As a tweener, NWA Champion Flair retained the gold over Nikita Koloff inside a cage, and Koloff’s comrades laid a beatdown afterward. Rhodes made the save on his enemy’s behalf as an act of conciliation. Rather than accept the gesture, Flair allowed Ole and Arn Anderson to jump Dusty, and the three broke his ankle inside the locked cage. If Flair’s allegiance was on the fence before the day, he ended it as the top heel once more.

9. Marty Jannetty Eats Glass (December 3, 1991)

Legendary for the unique moment of Shawn Michaels propelling Jannetty through the window of The Barber Shop, and Jannetty blading on what was generally family programming. Had Jannetty not been temporarily let go after a police altercation in early 1992, the planned blowoff at WrestleMania VIII could’ve been epic. Still, it set Michaels in motion to become one of wrestling’s greatest stars.

8. Vince McMahon Embraces the Hate (April 13, 1998)

Hard to pin down the exact moment Vince became classified as ‘heel’, but post-Montreal, McMahon started to dance around the fire with simple remarks toward Steve Austin, including his wish that Austin not become the WWE Champion. After a pair of run-ins with Austin post-WrestleMania, McMahon accepted Austin’s challenge for a match on the Raw that turned the ratings tide against WCW, and “Mr. McMahon” became one of wrestling’s greatest villains.

7. Larry Zbyszko Betrays Bruno Sammartino (January 22, 1980)

Sammartino was wrestling royalty in WWE, and protege Zbyszko couldn’t get out of his shadow. During an exhibition match between teacher and student, Sammartino gamely outwrestled his younger opponent, much to Zbyszko’s frustration. Once thrown to the floor, Zbyszko returned with a chair, and bashed it over Bruno’s head, leaving him laying in his own blood. In real life, Zbyszko had his life threatened by numerous fans in the Northeast, before paying off the feud with a cage match at Shea Stadium.

6. The Freebirds Annihilate Kerry Von Erich (December 25, 1982)

Michael Hayes was chosen to be guest enforcer for Ric Flair’s NWA World Title defense against Von Erich, held inside a steel cage in Dallas, TX; true Von Erich territory. Late in the match, Hayes laid out Flair for Von Erich’s benefit, but Kerry wouldn’t accept the cheap win. Von Erich went for the door, only for Hayes’ cohort Terry Gordy to slam the door on his head. Von Erich failed to win the gold, and the Freebirds-Von Erichs long rivalry was ignited.

5. Paul Orndorff Clotheslines Hulk Hogan (June 24, 1986)

Friends ever since Orndorff turned face in the spring of 1985, Hogan and Orndorff would team a number of times in rivalry with Roddy Piper, Bob Orton, and others. When Orndorff began to show signs of jealousy, and a missed phone call to Hulk made Orndorff look bad, the two put aside differences for a match with King Kong Bundy and Big John Studd. Post-match, Orndorff clotheslined Hogan, and then piledrove him, kicking off a mega-feud for the WWE Championship.

4. Terry Funk Murders Ric Flair (May 7, 1989)

Flair was just minutes removed from regaining the NWA Title, concluding his iconic trilogy with Ricky Steamboat, when Funk (serving as a ringside judge in the event of a draw) forcibly asked for a title shot. When Flair dismissed him, albeit with some regard, as not among the next batch of contenders, Funk’s ‘apology’ for the intrusion was to wallop Flair, and piledrive him through the judge’s table at ringside. The two would war through the remainder of 1989.

3. The Mega Powers Explode (February 3, 1989)

In one of the most extensively-subtle performances in wrestling history, Savage would show slight discomfort at Hogan’s kind treatment of Miss Elizabeth, no matter how innocent. Additonally, jealousy of Hogan’s popularity factored into Savage’s deteriorating mental state. Finally, during a match with the Twin Towers, Hogan tended to the injured valet, and Savage finally lost it, exploding with a hate-filled tirade at a stunned Hulk, before nailing him with the WWE belt in front of a pained Liz.

2. Andre the Giant Confronts Hulk Hogan (January 26, 1987)

Upset at playing second fiddle to a ceremony for Hogan’s three-year championship reign, Andre walks off, only to return weeks later on Piper’s Pit with Bobby Heenan as his new manager. Andre calmly told an astonished Hogan that he had only one thing to demand: a World Title match at WrestleMania III. Hogan tried to reason with Andre, who callously ripped Hogan’s shirt and crucifix jewel off in response. The result was one of the most historic and important wrestling matches in history.

1. Hulk Hogan is “The Third Man” (July 7, 1996)

This time, it’s Hogan doing the turning. After Scott Hall and Kevin Nash invaded WCW in the spring of 1996, they promised a hostile takeover, and the addition of a third man. At Bash at the Beach, during the anticipated main event where that man would be revealed, Lex Luger was injured, leaving Sting and Randy Savage alone with The Outsiders. Hulk Hogan appeared to make the save, only to leg drop Savage, and reveal his treachery. Hogan’s post-match speech, denouncing WCW and the fans that turned on him, while announcing the formation of the New World Order, is the greatest promo of his iconic career, and that’s saying something.

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